Janine Entertains Two Gentlemen

Janine has always had lots of boyfriends but has never wanted to settle on any one guy. They come and go in a year at most, and generally she has several on hold at any one time. She would tell you it's because guys like redheads, but of course there is more to it than that. She's vivacious, outgoing and is attracted to many different types of guys. At any social gathering Janine chat up and flirt with any but the most obnoxious guys. When it comes to boyfriends, though, she's pretty picky -- she can afford to be -- but she does tend to see everyone's good points.

She works as a nurse, but unlike many nurses, prefers not to date doctors, except those rare ones who can avoid talking about work. She knows she'll never get rich as a nurse, but will never be unemployed, and she loves the freedom of moving from place to place every few years without worrying too much about job prospects.

Janine has always been a little obsessed with group sex -- threesome, foursomes, whatever, but also aware of the practical difficulties. Still she always thought that she could handle and enjoy several guys together.

The first time she acted on her fascination was a fairly modest attempt with two guys, which nonetheless made her appreciate how complicated the emotions can be, even with men. She'd been dating two different guys, who I'll call Bart and Matt, and in typical Janine style, they knew about each other, but had not actually met. She would never rub it in her guys' faces when she was seeing someone else, but didn't deny it either, honest enough to never tell a guy he was the one and only.

She had decided to make her move because she actually thought that these two would like each other, naively failing to fully appreciate the strong rivalry they would naturally feel, no matter how much else they had in common. With a bit of insistence she got them to agree to come over to her house together for dinner. Both of them were expecting some drama scene where one or both would get dumped. What else could it be?

Bart thought it might be good strategy to arrive early to find out what was going on and then leave if it looked bad, but then he was surprised to find her dressed in nothing but a thong and an apron, putting the finishing touches on dinner. She seemed happy he was there, gave him a long, sexy kiss with lots of tongue while she grabbed his ass, pushing his crotch into hers, before going to get him a drink. So naturally he figured the other guy would be the loser in whatever was going on.

By the time Matt arrived Janine had taken off the apron, so he got greeted by Janine in her thong and also got an intense kiss while Janine pushed her bare breasts against his chest and ran her hand over his crotch. When she brought Matt his drink, her hand passed over Bart's ass. After a bit of small talk she said, "Guess I don't really need this to have dinner with two lovers," and stepped out of her thong.

The two had a lovely dinner with naked Janine who kept talking about the accomplishments of her two lovers. Of course, each liked hearing her talk about him, but bored and annoyed to hear of the other. When she excused herself for a few moments, the two, despite their natural rivalry over the same hot woman, just looked at each other quizzically and shrugged their shoulders, then waited silently for her return, not sure if she could hear them.

That absence had been for Janine's second enema of the day. This might have been overkill, but her experience with anal intercourse had been limited, and she wanted it pleasant for these guys, assuming she'd be able to get them into this. She was having her doubts, having begun to sense the tension between the two.

Janine thought that the guys would have realized by now what she was up to, so she took the direct approach, standing naked in front of them, her finger toying with her clit, inviting them to undress and join her in her bedroom. Both of them were clueless and froze staring at beautiful naked Janine, not knowing what to do. Either one would have stripped and joined her in a second, but with another guy there?

At this point it all got strange. Janine had to be more explicit about what she wanted than she had thought necessary, while the guys were vague about their reluctance. They didn't really want to undress in front of each other, although neither would actually come out and admit it, so it all took a while.

Finally she got them into bed, but it was all much more self-conscious than it should have been for three naked people getting ready for sex. Matt watched with obvious boredom, as Janine put Bart on his back, and took his long dick in her mouth for a few licks, before sheathing it in a condom and mounting him. And God did she love having that long unit finally slide into her and couldn't resist a few in-and-outs despite Matt's annoyance. She was tempted to just kept going and just fuck Bart in front of Matt, who was being such an asshole, but she finally forced herself to keep her mind on her goal.

Matt played dumb and insisted on being told exactly what to do - lube her asshole well, put on a condom and insert himself slowly and gently, letting her asshole expand. For sure it hurt Janine a bit, but once he was in she loved the fullness and began moving back and forth between her two lovers. Neither wanted their balls, hands or legs to touch, but of course they did, and as they got further into their mutual fuck, it got harder to worry about. Matt loved the tightness of Janine's anus, as she stroked back and forth, and had to hold back, not wanting to come before either of them, so he could show that he was the better lover. Bart was having a hard time holding still lying on his back and letting Janine do the stroking, but he did get used to it and began enjoying her deliberate movement. Janine thought it was all more awkward than she had thought, but it did get more and more exciting, finally fucking two guys at once, and she soon realized that she was about to cum. She didn't give in, trying to drag it out a little longer, enjoying this rare occasion with two sexy guys inside her, plus the control of doing all the moving.

The guys both noticed as she began to let out short, high-pitched cries that neither had hear before, reassuring both that the extra penis in her anus wasn't hurting her and exciting both with her obvious pleasure. Matt thought he could hold on no longer in Janine's tight little asshole, but Bart was a bit behind, when Janine began the shouts which both recognized as coming just before a major climax. Matt was just about as vocal as Janine, which sort of shut down Bart, leaving him unsatisfied when Janine disengaged from both.

Janine rolled over on her back, happy but still aroused, when Bart mounted her to finish in the missionary position, definitely making Matt feel left out, especially since they took what seemed a long time. Janine's pleasure was obvious when she came with Bart.

Neither of her beaux said anything, but Janine sensed the resentment. The encounter had been good for her sexually, but emotionally somewhat disappointing.

She sensed that neither would leave before the other, although neither was comfortable, and she definitely considered kicking them out, but decided to suggest they have a few drinks and watch some videos. Both guys got more or less dressed in their underwear, but Janine stayed naked. The videos turned to soft porn and the drinks to dope. Seeing Janine's taste in porn, the guys began to understand what had just happened. Watching her favorite videos Janine had slowly begun touching herself and then openly masturbating when the guys took over. Four hands on her clit, inside her vagina and on her tits got her moving, and in her excitement she pulled down Matt's briefs to take his penis in her mouth, even without a condom, and sucking him to climax at the same time as Bart's skillful finger fucking got her off. After catching her breath and getting Matt's cum out of her mouth she asked to do it again, and this time took Bart in her mouth, while Matt fingered her into the stratosphere.

Against their wills the two guys were beginning to understand cooperation, having really enjoyed ejaculating in Janine's mouth, while she was having her own orgasm. Still each would have preferred to have Janine to himself. Both agreed with her suggestion to spend the night, mainly so as not to let the other have her alone.

Janine slept between the two, getting them both very close to her, and grabbing a handful of their packages from time to time. Bart slept longer and was awakened by Matt and Janine talking. laughing and kissing. Matt was on top of her, and about to stick his cock in her. Janine saw Bart wake and slipped out from under Matt and, to Bart's annoyance got on top of Matt, kissing him and grinding her pussy against his erect cock.

While still laying on top of Matt, she grabbed Bart's dick and announced she wanted to play "musical fucking." "I'm going to put some pillows at the foot of the bed, and lie over them. I want each of you stand behind the bed and fuck me until I cum, then I want the next to take over until I cum again, and so on until you each cum. Hold on as long as you can. Each of you can choose if you want me face up or down."

The two flipped coins and Bart started, asking her to lie face up. She got into it very fast, but Bart was spent from fucking her twice the evening before, and it was easy to hold out. She was moaning, thrashing, and calling for Matt, before he had even warmed up. Matt had her roll over and fucked her doggy style, while Bart stood there watching with his stiff, unsatisfied cock. She came even faster with Matt, so Bart took over, staying with the position from behind. Bart lasted through three sessions, Matt four, and amazingly Janine came every time. Janine was satisfied, Bart jealous, and Matt proud of his endurance.

She suggested that they shower together, but Bart said he needed to get home and would shower there. Matt stayed for a shower and breakfast with Janine, but left soon. After that she didn't hear from Bart for two weeks, so she called him to invite him to go out, but he had an excuse, so she let it go. She saw Matt fairly often for about a month, but that relationship ended with a major fight during a sleepover at her house, and one of the problems he kept mentioning was "the humiliating night with her other lover."

Janine was more interested in multiple partners than ever, but realized she needed to make it less personal for her playmates, avoiding guys who might be thinking of her in romantic terms. Having more guys would help to depersonalize it, as well as increase the thrill.